Richard would serve as an officer in the Marines during World War I. After his service was over he went to Princeton University and graduated from there in 1919. After his graduation he went on to study law at Harvard Law School where he graduated in 1924. He became a successful lawyer in Baltimore and lived in the city his entire life.

In 1967 he became a delegate to the Maryland state constitutional convention.

Cleveland passed away in Baltimore and was buried in Carroll County, NH. His sister Esther was buried near him when she died six years later.